(1R,2S,5R)-(-)-8-phenylmenthyl chloroformate | 126378-43-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2S,5R)-(-)-8-phenylmenthyl chloroformate
• 英文别名: (-)-8-phenylmenthyl chloroformate；(-)-8-phenylmenthol chloroformate；(1R,2S,5R)-5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexyl carbonochloridate；[(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] carbonochloridate
• CAS: 126378-43-6
• 化学式: C₁₇H₂₃ClO₂
• 分子量: 294.821
• InChiKey: MGFZWSCAFUWZSB-BPLDGKMQSA-N

物化性质

• 沸点：
  363.4±9.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2S,5R)-(-)-8-phenylmenthyl chloroformate 在 sodium tetrahydroborate 、 cerium(III) chloride 、 三氟化硼乙醚 、 水 作用下， 以 甲醇 为溶剂， 反应 0.08h， 生成 (S)-4-hydroxy-1-((1R,2S,5R)-8-phenylmenthoxycarbonyl)-(S)-2-triphenylsilyl-1,2,3,4-tetrahydropyridine
  参考文献：
  名称：

  Stereoselective addition of (triphenylsilyl)magnesium bromide to chiral 1-acyl-4-methoxypyridinium salts. Synthesis and reactions of enantiopure 1-acyl-2-(triphenylsilyl)-2,3-dihydro-4-pyridones

  摘要：

  DOI：

  10.1021/ja00053a050
• 作为产物：
  描述：

  长叶薄荷酮 在 吡啶 、 copper(I) bromide 、 sodium 、 异丙醇 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (1R,2S,5R)-(-)-8-phenylmenthyl chloroformate
  参考文献：
  名称：

  Total Synthesis of (−)-Epibatidine Using an Asymmetric Diels−Alder Reaction with a Chiral N-Acylnitroso Dienophile

  摘要：

  An asymmetric total synthesis of(-)-epibatidine (1), isolated from the skin of the Ecuadorian poison frog, Epipedobates tricolor, of the family Dendrobatidae, has been achieved by virtue of the development of asymmetric hetero Diels-Alder (D-A) cycloaddition with an N-acylnitroso dienophile bearing the optically active 8-arylmenthol as a chiral source. Thus, in situ oxidation of the hydroxamic acid ent-laf incorporating the (1S,2R,5S)-8-(2-naphthyl)menthyl auxiliary was performed using the Swern conditions to produce the acylnitroso dienophile, which reacted at once with 2-chloro-5-(1,5-cyclohexadienyl)pyridine (7) to provide the (1S,4R)-meta-aza cycloadduct 24 as a major diastereoisomer. The observed facial diastereoselectivity is consistent with a transition-state model with the naphthyl group in "stacked" position and with the acylnitroso group in the s-cis conformation, wherein pi attractive interaction between the naphthyl and nitrosocarbonyl groups may contribute to facial control. Compound 24 underwent hydrogenation followed by removal of the chiral auxiliary with LiH2NBH3 and reductive cleavage of the N-O bond with Mo(CO)(6) to give the amino alcohol derivative 29, which was converted to (-)-epibatidine via bromination followed by cyclization.

  DOI：

  10.1021/jo9813078
• 作为试剂：
  描述：

  8-(3-Bromo-4-fluorophenyl)-10,10-dioxo-5-oxa-10lambda6-thia-2-azatricyclo[7.4.0.03,7]trideca-1(9),3(7)-dien-6-one 在 potassium tert-butylate 、 (1R,2S,5R)-(-)-8-phenylmenthyl chloroformate 、 sodium methylate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以210 mg的产率得到(+)-9-(3-bromo-4-fluorophenyl)-3,4,6,9-tetrahydro-2H-furo[3,4-b]thiopyrano[2,3-e]pyridin-8(5H)-one 1,1-dioxide
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of a Novel Series of Tricyclic Dihydropyridine-Based K_ATP Openers That Potently Inhibit Bladder Contractions in Vitro

  摘要：

  Structure-activity relationships were investigated on a novel series of tricyclic dihydropyridine-containing K-ATP openers. This diverse group of analogues, comprising a variety of heterocyclic rings fused to the dihydropyridine nucleus, was designed to determine the influence on activity of hydrogen-bond-donating and -accepting groups and their stereochemical disposition. Compounds were evaluated for K-ATP activity in guinea pig bladder cells using a fluorescence-based membrane potential assay and in a pig bladder strip assay. The inhibition of spontaneous bladder contractions in vitro was also examined for a subset of compounds. All compounds studied showed greater potency to inhibit spontaneous bladder contractions relative to their potencies to inhibit contractions elicited by electrical stimulation.

  DOI：

  10.1021/jm030357o

文献信息

• Chelate-Controlled Asymmetric Synthesis of 2-Substituted 2,3-Dihydropyridin-4(1H)-ones: Synthesis ofD- andL-aminodeoxyaltrose derivatives
  作者：Jacques Streith、Arnaud Boiron、Jean-Louis Paillaud、Elsa-Maria Rodriguez-Perez、Christiane Strehler、Th�ophile Tschamber、Margareta Zehnder

  DOI：10.1002/hlca.19950780106

  日期：1995.2.8

  Asymmetric methylation and phenylation of the chiral pyridinium salt 7, as well as methylation of chiral pyridinium salt 18, with Grignard reagents occurred in good yield and with good-to-excellent diastereoselectivities (Schemes 2 and 3, resp.). These results are best explained by assuming chelate control to govern the asymmetric alkylation/arylation process. The minimum-energy conformations of the

  不对称甲基化和手性的吡啶鎓盐的苯基化7，以及手性的吡啶鎓盐的甲基化18，与格氏试剂发生在良好的产率和具有良好至优秀非对映选择性（方案2和3，RESP）。通过假定螯合剂控制非对称烷基化/芳基化过程，可以最好地解释这些结果。由“分子模拟Cerius-Dreiding II”程序确定的面外扭曲吡啶鎓盐7和18的最小能量构象与假定的不对称螯合物控制机制高度吻合。
• Asymmetric Synthesis of 2-Alkyl(Aryl)-2,3-dihydro-4-pyridones by Addition of Grignard Reagents to Chiral 1-Acyl-4-methoxypyridinium Salts
  作者：Daniel L. Comins、Sajan P. Joseph、R. Richard Goehring

  DOI：10.1021/ja00090a019

  日期：1994.6

  Grignard addition to a chiral 1-acyl-4-methoxypyridinium salt provides synthetically useful 2-alkyl(aryl)-2,3-dihydro-4-pyridones in high diastereomeric excess

  格氏加成到手性 1-酰基-4-甲氧基吡啶鎓盐提供合成有用的高非对映体过量的 2-烷基（芳基）-2,3-二氢-4-吡啶酮
• DIHYDROPYRIDONE UREAS AS P2X7 MODULATORS
  申请人：Brotherton-Pleiss Christine E.

  公开号：US20100160388A1

  公开（公告）日：2010-06-24

  Compounds of the formula I: or pharmaceutically acceptable salts thereof, wherein m, n, R 1 , R 2 , R 3 , R 4 and R 5 are as defined herein. Also disclosed are methods of making the compounds and using the compounds for treatment of diseases associated with the P2X7 purinergic receptor.

  公式I的化合物：或其药用可接受的盐，其中m、n、R1、R2、R3、R4和R5按本文件定义。还公开了制造这些化合物的方法以及使用这些化合物治疗与P2X7嘌呤能受体相关疾病的方法。
• DIHYDROPYRIDONE AMIDES AS P2X7 MODULATORS
  申请人：Lopez-Tapia Francisco Javier

  公开号：US20100160387A1

  公开（公告）日：2010-06-24

  Compounds of the formula I: or pharmaceutically acceptable salts thereof, wherein m, n, R 1 , R 2 , R 3 , R 4 and R 5 are as defined herein. Also disclosed are methods of making the compounds and using the compounds for treatment of diseases associated with the P2X7 purinergic receptor.

  式I的化合物： 或其药用可接受的盐，其中m、n、R1、R2、R3、R4和R5如本文所定义。还公开了制备这些化合物的方法，并将这些化合物用于治疗与P2X7嘌呤受体相关的疾病。
• Pyrano, piperidino, and thiopyrano compounds and methods of use
  申请人：Abbott Laboratories

  公开号：US06642222B2

  公开（公告）日：2003-11-04

  The present invention provides novel compounds of formula I which may be useful in hyperpolarizing cell membranes, opening potassium channels, relaxing smooth muscle cells, and inhibiting bladder contractions.

  本发明提供了一种公式I的新化合物，可能在超极化细胞膜、打开钾通道、放松平滑肌细胞和抑制膀胱收缩方面有用。